In this episode of the iGaming Leader Podcast, Leo sits down with Kyle Wiltshire, the founder and CEO of TESTA. Kyle takes us on a journey from the high-octane "Wild West" days of Bodog in Manila to building a global, bootstrapped testing powerhouse from his base in Taipei.

Kyle shares the "brutal" reality of scaling an operation from 50 to 1,200 people in a flash, the hard-learned lessons of dealing with technical partners who try to "hold products hostage," and why he believes the common corporate trope of "we are a family" is actually toxic for performance. He opens up about his philosophy of "making yourself non-essential" and why the most successful leaders are generalists who know exactly when to hand off the ball.

GUEST BIO

Kyle Wiltshire
Founder & CEO, TESTA

Kyle Wiltshire is a technical-leader-turned-entrepreneur who specialised in DevOps and backend innovation long before they were buzzwords. After years of driving massive scalability for Asia-facing operators, he founded TESTA in 2023 to solve a persistent industry pain point: real-world, crowdsourced QA for the global iGaming sector. Based in Taipei, Kyle is a self-proclaimed "generalist" with an MBA who believes in building lean, profitable businesses in uncontested markets.

Key topics discussed

00:00 – Why a company is a sports team, not a family.
02:00 – Moving to Manila: The "brutal" 12-hour time difference and the project that never ended.
04:00 – The Bodog Days: Scaling from 50 to 1,200 people and the chaos of "two of everything."
09:00 – The Partner Betrayal: How a startup partner tried to hold code hostage for equity.
14:00 – The Ethics of Equity: Why Kyle is now "freewheeling" no more with cap tables.
16:00 – The Bootstrap Constraint: Why saying "no" to VC money made TESTA a more scientific business.
23:00 – Finding the "Blue Ocean": Why Kyle chose crowdsourced testing over the "Red Ocean" of slot studios.
26:00 – The Squeaky Wheel: Why coaching low performers is a drain on the high performers.
31:00 – Parroting vs. Execution: The challenge of "yes-men" in diverse global cultures.
36:00 – The Art of the Handoff: How to get over yourself and let the team run the booth.
43:00 – The Vince McMahon Lesson: Railroaded ambition and disrupting regional territories.

Key takeaways

The Sports Team vs. Family Model: A family is unconditional; a company is mission-based. Viewing your team as a high-performance sports unit allows for the "ruthless" but necessary decisions required to protect the organisation's goals.

Make Yourself Non-Essential: The ultimate goal of a founder is to be "off the critical path." If a business requires you to be the subject matter expert in every room, you haven't built a company—you've built a job.

The "Mom Test" for Software: You can have all the data in the world, but you will always learn more by watching a real person use your product in their own environment. Data tells you what is happening; stories tell you why.

Bootstrap for Clarity: Outside capital often forces a "race to the top" that ignores product-market fit. Spending "money that would have been in your pocket" forces a more disciplined, scientific approach to growth.

Stop Fixing People: In leadership, you cannot solve people like a technical challenge. Spending excessive time coaching a low performer isn't just a waste of your time—it’s an insult to your high performers who are actually carrying the weight.

Memorable quotes

"A company is not a family. Let's be honest, we're trying to accomplish this thing... It’s not, we're all just here to hug each other and sing Kumbaya."

"How would you ever get promoted if they absolutely need you to do the thing that you do? The goal is to make yourself not essential."

"If you are clever enough to build another slot company in 2026, good on you... I like the uncontested space."

"You have to learn to fire people when it’s not working because it’s actually this weird superpower that brings the whole group together."

Connect with Kyle Wiltshire:

https://www.testa.io
https://www.linkedin.com/in/kwiltshire/
https://next.io/podcasts/next-io-podcast/kyle-wiltshire-the-truth-about-doing-business-in-southeast-asia/

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LinkedIn: https://www.linkedin.com/in/leo-judkins/
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In this episode of the iGaming Leader Podcast, Leo sits down with Ian Freeman, a commercial powerhouse who has navigated the high-stakes world of Kambi, IGT, and Inspired Entertainment.

Ian pulls back the curtain on the "Bait and Switch" of executive leadership, the moments when the glossy job description meets the grim reality of a business in crisis.

Ian reflects on the formative trauma of losing his father at 20 and how carrying a family legacy forged a "survive and thrive" mentality that defined his career.

He shares the brutal honesty of walking into his first board meeting at a new firm only to realise the company was on the verge of insolvency, and how he learned, through painful trial and error, that coming in "too hot" can sometimes fuel the fire rather than put it out.

Key topics discussed

00:00 – The First Board Meeting: Realising there wasn't "another page" to the numbers.
03:00 – Formative Crisis: Losing a father at 45 and taking over the family legacy at 20.
07:00 – Breaking Down: The moment Ian realised he was living his father's life, not his own.
08:00 – Fishing with Ted Baker: Lessons in entrepreneurship from the riverbank.
10:00 – The "Moxie" Days: Learning the John McMahon sales toolkit.
13:00 – The Scandinavian Consensus: What iGaming can learn from Kambi’s leadership culture.
19:00 – Walking into Insolvency: How to lead when everyone's "hair is on fire."
24:00 – The Danger of "Coming in Hot": Why speed isn't always the answer in a turnaround.
28:00 – The Fear of Failure: Admitting when you need help in the C-Suite.
33:00 – The B2B Sin: Why failing to deliver technology is "killing" your customers' businesses.
40:00 – Living for Two: How Ian carries his father's legacy into the next 20 years of iGaming.

GUEST BIO

Ian Freeman, former CCO & CRO (Kambi, IGT, Inspired Entertainment), is a veteran commercial leader with over 20 years of experience across Europe, North America, and LatAm. From driving Kambi’s landmark IPO to navigating the complex regulatory waters of Brazil for Inspired, Ian has seen the industry from every angle. Beyond the boardroom, Ian is a devoted father in a blended family and a passionate fly fisherman who finds his clarity in the silence of nature.

Follow Ian Freeman on Linkedin: www.linkedin.com/in/free-man

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LinkedIn: https://www.linkedin.com/in/leo-judkins/
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In this episode of the iGaming Leader Podcast, Leo sits down with Elen Barber, who went from affiliate manager to CMO at Kindred in just nine years, to explore what it really takes to lead through the industry's toughest challenges.

Elen shares the brutal reality of her first weeks as CMO: facing a £100 million fine, Swedish re-regulation, plummeting share price, and multiple rounds of restructuring that forced her to make impossible decisions about people she'd worked alongside for years. She reveals how she kept 550 people motivated while simultaneously having to cut headcount, and why the loneliness at the top hit harder than she expected.

About Elen Barber

Elen Barber has been working in the gaming industry for over 20 years and has witnessed its evolution from the wild west days to today's highly regulated landscape. She's held CMO roles at Super Group and Kindred Group, managing teams across multiple countries and dealing with everything from new market launches to regulatory curveballs. Based in London, she's passionate about how this industry continues to reinvent itself.

Key Topics Discussed

00:00 - Elen Barbers iGaming Journey
03:00 - Creating your own opportunities: you can't wait for your manager
08:00 - Why the higher you go, the lonelier it gets (and how to handle it)
14:00 - Wearing different hats: the two-chair technique for managing emotions
18:00 - Building trust: having your team's back and showing your true nature
22:00 - The worst crisis in company history hits in week one as CMO
26:00 - Managing multiple restructures while keeping people motivated
34:00 - Life after Kindred: why career breaks aren't always roses
36:00 - The pressure of being a perfect parent, perfect exec, perfect everything
41:00 - Quick fire Q&A: leadership advice, mistakes, and legacy

Memorable Quotes

"It is too easy to make money in our industry comparing to any other industries. The margins are much higher. So we are spoiled for this. It doesn't drive innovation."

"You also create opportunities, you don't wait for the opportunities to be created for you. You can't rely completely on your manager to get you through your career."

"And it is scary for the leader to understand and accept that suddenly you know significantly less than people within your team."

"I've been working all my life, and I didn't know how to relax, I missed that mental stimulation. "

"You really have to try to take emotions out of the business decisions because these things do not work together."

Connect with Elen Barber

LinkedIn: https://www.linkedin.com/in/elen-barber/

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LinkedIn: https://www.linkedin.com/in/leo-judkins/
Newsletter: https://www.igamingleader.com/subscribe
Join the Mastermind: https://www.igamingleader.com/apply

In this episode of the iGaming Leader Podcast, Leo sits down with veteran executive David McDowell, co-founder of FSB Technology and an early pioneer in the B2B platform space, to unpack the brutal reality of the 30-year entrepreneurial journey.

David shares the truth about leadership burnout (it's the weight of the decisions, not the hours), the biggest mistake CEOs make when scaling (waiting too long to remove a talented but toxic employee), and the devastating cost of losing your vision.

He offers a raw, cathartic reflection on the final chapters of FSB: being named Platform of the Year, only to have the momentum killed by a lack of capital investment demanded by a board focused on short-term liquidity. This is a crucial lesson in battling the "noise to the vision" and the indispensable wisdom only gained by staying in the game long enough to get the wins.

About David McDowell

David started his career as an engineer in Michigan and moved to London to do an MBA in 1993. He launched his first business, a two-sided marketplace using college students to teach adults how to use the internet, in 1995. He has since spent 25 years in the gambling industry.

He co-founded GameAccount (now GAN), an early skill games provider that pivoted to B2B casino games and platform provider before its IPO in 2013.
He co-founded and was CEO for 15 years of FSB Technology, a B2B sports betting platform that was sold to PE in 2019 and on to EveryMatrix in 2024.

He currently works as an independent consultant with various gambling-related businesses and serves as an Entrepreneur Mentor in Residence at London Business School.

Key Topics Discussed

00:00 - The entrepreneurial philosophy
04:00 - Building the first venture (SOS) in 1995
06:15 - Transitioning to CEO: becoming the external face of the organisation
07:45 - It often feels like everything that you do is a mistake
10:00 - Managing burnout: the importance of compartmentalising and health
16:30 - Careful who your investors are
19:20 - The fundraising Goldilocks problem: minimising dilution while maximising runway
24:30 - Why customer-led features are often an absolute waste of time
31:00 - Knowing in your gut someone is wrong for the organisation
37:00 - Communicating your vision clearly
39:00 - Isolation in leadership
47:00 - What would I do differently going back

Memorable Quotes

"The entrepreneurial journey is just staying in the game long enough so that you can get the wins."
"All of those are almost noise to the vision. You still have to kind of make sure that you're building your own vision..."
"My biggest mistake is waiting too long [to remove a cultural mismatch] because I thought we need... we can't afford the disruption right now."

Connect with David McDowell

LinkedIn: https://www.linkedin.com/in/david-mcdowell-547209?lipi=urn%3Ali%3Apage%3Ad_flagship3_profile_view_base_contact_details%3BomU134VSR%2B2eskLlRqTFHQ%3D%3D

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LinkedIn: https://www.linkedin.com/in/leo-judkins/
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Join the Mastermind: https://www.igamingleader.com/apply

In this episode of iGaming Leader, Leo sits down with William J. Pascrell III, “BP3”. He is a partner at Princeton Public Affairs Group and a driving force behind the legalisation of sports betting and online gaming in the United States.

BP3 shares the unseen cost of bold bets: losing every major client when he onboarded PokerStars to help bring iGaming to America, the two-year sprint that followed, and the resilience forged long before politics from a 45-day coma with spinal meningitis to the daily discipline learned from his father.

This is a conversation about courage, people, and choosing to be a happy warrior rather than an angry gladiator.

About BP3

Bill Pascrell III is a veteran strategist and lobbyist who helped lead New Jersey’s iGaming framework and the decade-long campaign that culminated in PASPA’s repeal in 2018.

He advises governments and gaming companies across the US and internationally on policy, compliance and market access.

Key Topics Discussed

00:00 – Scars, setbacks and the “small gladiator” mindset
03:30 – “Architect of American sports betting” and what it really means
08:00 – Growing up without privilege and learning to outwork everyone
14:00 – Spinal meningitis as a teenager
20:00 – Lessons from his father on example, integrity and service
23:30 – The King David Hotel story and resourcefulness under pressure
28:30 – Grief, legacy and the Pascrell Public Service Institute
34:00 – Onboarding PokerStars, losing every client and starting again
39:00 – NFL opposition, real-world pressure and personal risk
40:00 – Happy warrior versus angry gladiator
43:00 – People before everything

Memorable Quotes

“I have the scars and the bruises to show I was a small gladiator in this fight.”

“Give me 10% of 40 million and I’ll get this done in two years. And we did.”

“I could have treated my adversaries more as a happy warrior than as an angry gladiator.”

“Titles come and go. What matters is how we treat each other.”

Connect with Bill Pascrell III

LinkedIn: https://www.linkedin.com/in/billpascrell/
X: https://x.com/BillPascrell3rd
INSTAGRAM:https://www.instagram.com/pascrell3rd/

Follow Leo Judkins & iGaming Leader

LinkedIn: https://www.linkedin.com/in/leo-judkins/
Newsletter: https://www.igamingleader.com/subscribe
Join the Mastermind: https://www.igamingleader.com/apply

Learn more about BP3

BP3 on Boston 25 News
https://www.boston25news.com/news/local/25-investigates-sports-betting-could-raise-odds-problem-gambling-ma/PSOWJETP6ZA4VAX24VQZFCQURI/

The Philadelphia Inquirer: Entain Foundation U.S. Educates Athletes on Sports Betting
https://www.inquirer.com/sports/nfl-ncaa-betting-education-entain-foundation-amani-toomer-20230727.html#loaded

BP3 for Pittsburgh Post-Gazette: Pennsylvania's Casinos Must Protect Problem Gamblers
https://www.post-gazette.com/opinion/Op-Ed/2022/11/28/racinos-betters-gambling-addiction/stories/202211280003

Forbes: How New Jersey Will Double Down on Gambling if Casinos Come to New York City
https://www.forbes.com/sites/willyakowicz/2022/10/14/how-new-jersey-will-double-down-on-gambling-if-casinos-come-to-new-york-city/
BP3: From NJ.com: NJ Sports Bettors Need More Protection
https://www.nj.com/opinion/2024/04/nj-sports-bettors-need-more-protection-opinion.html
Game Masters 2025: TOP 100 Most Influential Figures in the U.S. iGaming Industry
Game Masters 2025: TOP 100 Most Influential Figures in the U.S. iGaming Industry - USiGamingHUB
Sen. Addabbo: Legalize iGaming First, Then ‘I Want To Create’ Sweeps Regulation
Addabbo: Legalize iGaming, Then 'I Want To Create' Sweeps Regulation
Casinos, online play fuel strong July in NJ
Casinos, online play fuel strong July in NJ - NJBIZ
BP3: From IMGL Magazine– The Importance of Geolocation in the Online Gaming Industry
IMGL Magazine June 2025

Internet gaming, sports wagering pace February DGE report (updated)
Internet gaming, sports wagering pace February DGE report (updated) - NJBIZ
Bill Pascrell: US Election day warm up:
https://next.io/podcasts/next-io-podcast/bill-pascrell-us-election-day-warm-up/?utm_campaign=Daily%20Newsletter&utm_medium=email&_hsenc=p2ANqtz--thGRArZ3dvBERn9NoBY4lv0g8vB2vmx1uDcV5DecKSq-IXpITjwZ5BQ8Y2K1E1L1FtsB5UODaJ190VR9ISatxI2aSTCq25FCypCtUlLfYVSSP-xc&_hsmi=97835674&utm_content=97835674&utm_source=hs_email

In this episode of iGaming Leader, Leo sits down with Jovana Popovic Canaki, CEO of iGP and one of the few female leaders in the B2B iGaming space.

Jovana opens up about the emotional highs and lows of leadership, the hidden pressure of being “the strong one,” and the journey from intimidation and self-doubt to authentic, grounded leadership.

The conversation explores losing her belongings abroad and what it taught her about vulnerability, balancing work with family roles, early-career imposter feelings, learning to lead without wearing a “manager mask,” and the reality of being a woman advancing through a male-dominated industry.

Guest Bio

Jovana Popović Čanaki, known to most as Jovi, is the CEO of iGP, an iGaming platform, aggregator, and lottery provider.

With more than 15 years of experience in the industry, she’s helped shape some of its most recognizable brands from Aspire Global to ORYX Gaming. Today she leads iGP’s evolution from a single-platform provider into a trusted, full-suite partner for operators worldwide.

But what really defines Jovi is her belief that growth comes from people first. She’s known for leading with empathy, authenticity, and a strong sense of purpose, building teams where creativity, accountability, and trust go hand in hand.

At iGP, she continues to champion the company’s Be Purple mindset, a reminder to stay bold, curious, and human, guiding both her team and partners to build gaming experiences that inspire connection and progress.

Key Topics Discussed

00:00 – The loneliness and emotional swings of leadership
03:00 – Losing everything in a hotel lobby: vulnerability and perspective
07:00 – The myth of work–life balance as a CEO, parent and expat
15:00 – How her early years shaped her leadership style
20:00 – Doubt, intimidation, and learning to “push through”
32:00 – Wearing a “manager mask” and the cost of inauthenticity
40:00 – Women in leadership: the progress, challenges and realities
50:00 – Her advice to her younger self: stop doubting

Memorable Quotes

“Do what you believe in.”

“Why are you so afraid to show who you are? What’s the worst that can happen?”

“If you don’t have a little stage fright, you don’t care enough.”

Connect with Jovi

https://www.linkedin.com/in/jovanapopovic/

https://igamingbusiness.com/strategy/management/jovana-popovic-canaki-igp-leadership/

https://g3newswire.com/igp-a-transformative-year/

www.igpgaming.com

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LinkedIn: https://www.linkedin.com/in/leo-judkins/
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In this episode of iGaming Leader, Leo sits down with Daniel Brooks, dual founder and hands-on CEO of BetComply and Ridentify. Daniel shares how a thoughtful, mentor-first approach lets him scale two companies at once, trust strong operators, and stay composed when cashflow shocks or client pull-outs hit.

He explains how journalling, walking meetings, and “breathing through” crises turn panic into analytical problem-solving and innovation.

The conversation explores people-first leadership, letting go without losing control, choosing and backing the right operators, making brave pivots without losing your core, and building a personal resilience system that keeps you calm under pressure. Practical insights for founders, COOs, and execs across iGaming.

Guest Bio

Daniel Brookes is an experienced business strategist and leader in the iGaming and technology sectors, currently serving as CEO of both BetComply and Rdentify. Known for his expertise in regulatory compliance, operations, and innovative AI-driven player protection solutions, Daniel has been instrumental in scaling businesses and driving growth in complex, regulated markets.

He is recognised for his hands-on leadership style, strategic vision, and commitment to fostering collaborative, trust-first company cultures. Daniel’s work focuses on helping operators navigate the challenges of compliance while promoting responsible gaming and customer protection.

Key Topics Discussed

00:00 – Thoughtful leadership: mentor first, megaphone second
03:00 – From hands-on Ops to true COO
05:00 – Letting go the right way: trust, verify, then back your best people
09:00 – Culture design: speed, iteration, low bureaucracy, clear process
12:00 – Running two companies: vision, operators, repeatable model
16:00 – “Breathe through it”: journalling and calm thinking in a crisis
19:00 – Private GPTs, writing, and structured reflection as a coping system
22:00 – Proud moments: team growth, fast KPIs, shared wins
31:00 – Founders, focus, and plate-spinning: why this isn’t “the Daniel show”
35:00 – Mentors who challenge vision and expand ambition
40:00 – Disruption mindset: ask bigger questions, push for better
41:00 – Family, holidays, and work–life choices that reduce stress
42:00 – Final advice: hire great people, move fast, know when to stop

Memorable Quotes

“Lead from the top, not in the weeds. Trust the team to deliver.”
“The only way through it is to breathe through it.”
“Ask better questions: how do we disrupt and make this the best it can be?”
“Don’t let anybody tell you to follow your dream if everything is saying no. Use those noes to realign.”

Connect with Daniel:

https://betcomply.com/
https://rdentify.com/
https://www.rdentifyconnect.com/
https://thoughteconomics.com/
https://www.linkedin.com/in/daniel-brookes-367b5b14/

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